DE1469707A1 - Process for dyeing structures made of polyesters or cellulose triacetate - Google Patents
Process for dyeing structures made of polyesters or cellulose triacetateInfo
- Publication number
- DE1469707A1 DE1469707A1 DE19641469707 DE1469707A DE1469707A1 DE 1469707 A1 DE1469707 A1 DE 1469707A1 DE 19641469707 DE19641469707 DE 19641469707 DE 1469707 A DE1469707 A DE 1469707A DE 1469707 A1 DE1469707 A1 DE 1469707A1
- Authority
- DE
- Germany
- Prior art keywords
- polyesters
- cellulose triacetate
- dyeing
- structures made
- chloroethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000004043 dyeing Methods 0.000 title claims description 7
- 229920002284 Cellulose triacetate Polymers 0.000 title claims description 5
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 title claims description 5
- 229920000728 polyester Polymers 0.000 title claims description 5
- 239000000975 dye Substances 0.000 claims description 11
- 239000000986 disperse dye Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical class OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KZYAYVSWIPZDKL-UHFFFAOYSA-N 1,4-diamino-2,3-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(Cl)C(Cl)=C2N KZYAYVSWIPZDKL-UHFFFAOYSA-N 0.000 description 1
- BMMNUXLWZAHXNL-UHFFFAOYSA-N 3-benzyl-2-phenylphenol Chemical compound C=1C=CC=CC=1C=1C(O)=CC=CC=1CC1=CC=CC=C1 BMMNUXLWZAHXNL-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- FODHIQQNHOPUKH-UHFFFAOYSA-N tetrapropylene-benzenesulfonic acid Chemical compound CC1CC11C2=C3S(=O)(=O)OC(C)CC3=C3C(C)CC3=C2C1C FODHIQQNHOPUKH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65131—Compounds containing ether or acetal groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/36—Material containing ester groups using dispersed dyestuffs
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/38—Preparing azo dyes on the material
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
Description
Bk/Ed \ Ό *·* ^S^ Bk / Ed \ Ό * * * ^ S ^ LlVimUSIN-BiyeiwerkLlVimUSIN-Biyeiwerk
Verfahren zum Procedure for Färben von, Gebilden aus PolyesternDyeing of, structures made of polyesters oder or CellulosetriacetatCellulose triacetate
Die vorliegende Erfindung betrifft ein Verfahren zum Färben von Gebilden aus Polyestern oder Cellulosetriacetat mit Diepersionsfarbstoffen oder Entwicklungsfarbstoffen. Das Verfahren besteht darin, dass man das Färben in Gegenwart von fl-Chloräthyl-chlorphenyläthern der FormelThe present invention relates to a process for dyeing structures made of polyesters or cellulose triacetate with dispersion dyes or developing dyes. The method consists in that the dyeing in the presence of fl-chloroethyl chlorphenyläthern of formula
0-CH2-CH2Cl
(Cl)n 0-CH 2 -CH 2 Cl
(Cl) n
in der η eine Zahl von 1 bis 5 ist, durchführt.in which η is a number from 1 to 5.
Geeignete Äther sind z.B. ß-Chloräthyl-4-chlorphenyläther, ß-Chloräthyl^^-dichlorphenyläther, ß-Chloräthyl-2,6-dichlorphenyläther, fl-0hloräthyl-2,4,6-trichlorphenyläther und ß-Chloräthyl-pentachlorphenyläther. Besonders bewährt hat sich die Mischung aus ß-Chloräthyl-dichlorphenyläthern, die erhalten wird, wenn man Äthylenchlorid mit einer alkalischen Lösung von Dichlorphenflen, wie sie bei der Chlorierung von Phenol anfallen, umsetzt. Ie A 9089 Suitable ethers are, for example, ß-chloroethyl-4-chlorophenyl ether, ß-chloroethyl ^^ - dichlorophenyl ether, ß-chloroethyl-2,6-dichlorophenyl ether, fluoroethyl-2,4,6-trichlorophenyl ether and ß-chloroethyl-pentachlorophenyl ether. The mixture of ß-chloroethyl dichlorophenyl ethers, which is obtained when ethylene chloride is reacted with an alkaline solution of dichlorophenols, such as those obtained in the chlorination of phenol, has proven particularly useful. Ie A 9089
909844/1628909844/1628
U69707U69707
Das erfindungsgemässe Verfahren gestattet, Gebilde, z.B. Fäden, Pasern, Gewebe und Folien, aus Polyestern vom Polyäthylenglykolterephthalat-Typ oder aus Cellulosetriacetat mit Dispersionefarbstoffen oder Entwicklungsfarbstoffen in tiefen Tönen unter erheblicher Beschleunigung der Farbstoffaufnähme zu färben.The inventive method allows structures, e.g. threads, Pipes, fabrics and foils made from polyesters of the polyethylene glycol terephthalate type or from cellulose triacetate with disperse dyes or to dye developing dyes in deep tones with considerable acceleration of dye uptake.
Die erforderlichen Mengen an den erfindungsgemäss zu verwendenden Äthern lassen sich durch Vorversuche von Fall zu Fall leicht ermitteln; im allgemeinen erweisen sich Mengen von 1 bis 5 g pro Liter Färbeflotte je nach der gewünschten Tiefe der Ausfärbung als ausreichend.The required M e nts to the present invention to be used ethers can easily be determined by preliminary tests on a case by case; In general, amounts of 1 to 5 g per liter of dye liquor are found to be sufficient, depending on the depth of coloration desired.
Da die Äther wasserunlöslich sind, ist dafür zu sorgen, dass sie im Färbebad in emulgierter Form vorliegen; zu diesem Zweck kann man sie in Form von Lösungen in organischen Lösungsmitteln, z.B. in heissem Alkohol, zu den Färbebädern, die einen Emulgator oder ein Emulgatorgemisch enthalten, zusetzen; man kann aber auch so vorgehen, dass man den Färbebädern Mischungen aus den Äthern und Emulgatoren zusetzt. Als Emulgatoren kommen vor allem anionaktive und nichtionogene Verbindungen in Betracht.Since the ethers are insoluble in water, it must be ensured that they are present in the dyebath in emulsified form; to this end they can be added to the dye baths in the form of solutions in organic solvents, e.g. in hot alcohol contain an emulsifier or an emulsifier mixture, add; but you can also proceed in such a way that mixtures of the ethers and emulsifiers are added to the dyebaths. as Particularly suitable emulsifiers are anionic and nonionic compounds.
Geeignete Dispersionsfarbstoffe und EntwicklungsfarbstoffeSuitable disperse dyes and developing dyes
sind z.B. in Diserens, "Die neuesten Fortschritte in derare e.g. in Diserens, "The latest advances in the
Anwendung der Farbstoffe", 2. Band, 2. Auflage, (1949),Application of the dyes ", 2nd volume, 2nd edition, (1949),
Seite 254 ff. bzw. 1. Band, 2. Auflage, (1946), Seite 304 ff.Page 254 ff. Or 1st volume, 2nd edition, (1946), page 304 ff.
beschrieben.described.
909844/1628909844/1628
Fasern aus Polyäthylenglykolterephthalat werden im Flottenverhältnis li40 zwei Stunden bei 96 - 980C in einem Bad bewegt, welches im Liter 0,75 g A-Zpchinon, 2 g Natriumoleoyl-methyl-taurid und 5 g der nachstehend beschriebenen Mischung enthält. Anschliessend werden die Fasern gespült und getrocknet. Man erhält eine tiefe Blau-Polyethylene glycol terephthalate fibers are in a liquor ratio li40 for two hours at 96 - 98 0 C moves in a bath containing, per liter, 0.75 g A-Zpchinon, 2 g Natriumoleoyl-methyl-tauride and 5 of the mixture described below contains g. The fibers are then rinsed and dried. You get a deep blue
färbung mit ausgezeichneter Lichtechtheit.coloring with excellent lightfastness.
Die eingesetzte Mischung hatte folgende Zusammensetzung! 50 Gewichtsprozent ß-Chloräthyl-dichlorphenyläther, erhalten durch Umsetzung von Äthylenchlorid mit einer alkalischen Lösung von Dichlorphenolen, wie sie bei der Chlorierung von Phenol anfallen, 8,8 Gewichtsprozent des Monoäthanolaminsalzes der Tetrapropylenbenzolsulfonsäure, 6 Gewichtsprozent des Umsetzungsproduktes aus 1 Mol Benzyl-phenyl-phenol und 16 Mol Äthylenoxid, 3,2 Gewichtsprozent Xylol und 32 Gewichtsprozent Wasser.The mixture used had the following composition! 50 percent by weight of ß-chloroethyl dichlorophenyl ether obtained by reacting ethylene chloride with an alkaline solution of dichlorophenols, as used in the chlorination of Phenol incurred, 8.8 percent by weight of the monoethanolamine salt of tetrapropylenebenzenesulfonic acid, 6 percent by weight of the reaction product of 1 mole of benzyl-phenyl-phenol and 16 moles of ethylene oxide, 3.2 percent by weight of xylene and 32 percent by weight Water.
Verwendet man ein Färbebad, welches anstelle von 0,75 g 4—/p-ToluidinpZ-l-oxyanthrachinon 0,5 g.l-Amino-2-brom-4-oxyanthrachinon oder 0,5 g l,4-Diamino-2,3-dichlor-anthrachinon enthält, so erzielt man bei sonst gleicher Arbeitsweise eine tiefrote bzw. violette lichtechte Färbung von ausgezeichneter Farbfülle und hervorragender Echtheit.If a dye bath is used which contains 0.5 g of 1-amino-2-bromo-4-oxyanthraquinone instead of 0.75 g of 4— / p-toluidine pZ-1-oxyanthraquinone or 0.5 g 1,4-diamino-2,3-dichloro-anthraquinone contains, a deep red or violet lightfast coloration of excellent color is achieved with otherwise the same procedure Full color and excellent authenticity.
909844/1628909844/1628
H69707H69707
•Pasern aus Polyäthylenglykolterephthalat werden im Flottenverhältnis Ii40 in ein wässriges Bad eingebracht, welches im Liter 0,75 g 4-/p-Toluidinq7-l-oxyanthrachinon und 2 g Natriumoleoyl-methyl-taurid enthält; das Bad wird dann auf 96 - 980C erwärmt und pro liter Flotte mit 2,5 g ß-Ohloräthyl-4-chlorphenyläther, gelöst in heissem Alkohol, versetzt. Anschlieseend werden die Pasern zwei Stunden bei 96 - 980O in dem Bad bewegt, hiernach gespült und getrocknet. Man erhält eine tiefe Blaufärbung mit ausgezeichneter Lichtechtheit.• Pipes made of polyethylene glycol terephthalate are introduced into an aqueous bath in the liquor ratio Ii40, which contains 0.75 g of 4- / p-toluidineq7-l-oxyanthraquinone and 2 g of sodium oleoylmethyl tauride per liter; the bath is then heated to 96 - 98 0 C and warmed per liter liquor 2.5 g ß-Ohloräthyl-4-chlorphenyläther dissolved in hot alcohol, was added. The fibers are then agitated for two hours at 96-98 0 O in the bath, then rinsed and dried. This gives a deep blue color with excellent light fastness.
Man verfährt wie in Beispiel 2 beschrieben, jedoch mit dem Unterschied, dass man der zum Färben verwendeten Flotte statt 2,5 g ß-Chloräthyl-4-chlorphenyläther 2,5 g ß-Ohloräthyl-2,4,6-trichlorphenyläther, gelöst in heissem Alkohol,zusetzt. Man erhält dann ebenfalls eine tiefe Blaufärbung mit ausgezeichneter Lichtecjitheit.The procedure is as described in Example 2, with the difference that instead of 2.5 g of ß-chloroethyl-4-chlorophenyl ether, 2.5 g of ß-chloroethyl-2,4,6-trichlorophenyl ether are dissolved in the liquor used for dyeing hot alcohol, adds. A deep blue color with excellent lightness is then also obtained.
"909844/1628"909844/1628
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0044368 | 1964-11-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1469707A1 true DE1469707A1 (en) | 1969-10-30 |
Family
ID=7100007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641469707 Pending DE1469707A1 (en) | 1964-11-04 | 1964-11-04 | Process for dyeing structures made of polyesters or cellulose triacetate |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE671360A (en) |
| DE (1) | DE1469707A1 (en) |
| DK (1) | DK111414B (en) |
| NL (1) | NL6514259A (en) |
-
1964
- 1964-11-04 DE DE19641469707 patent/DE1469707A1/en active Pending
-
1965
- 1965-10-25 BE BE671360D patent/BE671360A/xx unknown
- 1965-11-03 DK DK566365A patent/DK111414B/en unknown
- 1965-11-03 NL NL6514259A patent/NL6514259A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6514259A (en) | 1966-05-05 |
| DK111414B (en) | 1968-08-19 |
| BE671360A (en) | 1966-02-14 |
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